Abstract
Theoretical (B3LYP/6-31G*) and experimental (NMR, UV, and IR spectroscopy) data on the electronic and steric structure of 2-(2-benzoyl-1-phenylethenyl)-5-phenylpyrrole have been analyzed in the context of the hypothesis of the zwitter ionic nature of its ground state. The molecule involves a strong NH···O bond, and its ground state can be described as a hybrid of the neutral and zwitter ionic canonical forms; this conclusion was confirmed by the observation of a reversible medium effect on the electronic absorption spectrum of the substrate.
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Turchaninov, V.K., Chipanina, N.N., Stepanova, Z.V. et al. Solvatochromism of Heteroaromatic Compounds: XVIII. Reversible Effect of the Medium on the UV spectra of 2-(2-Benzoyl-1-phenylethenyl)-5-phenylpyrrole. Russian Journal of General Chemistry 73, 440–449 (2003). https://doi.org/10.1023/A:1024970222679
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DOI: https://doi.org/10.1023/A:1024970222679